Thanks to everyone for chiming in last week with the encouragement in this thread: https://www.indiehackers.com/forum/i-just-cold-called-5-prospects-for-the-first-time-holy-sh-t-was-it-hard-67cf35d22e
This week I increased to 6 cold dials. Some key takeaways:
Last week my pitch was forced, and I never let the prospect answer any questions before giving the whole thing. This week I took the advice from @wavve and opened with "Hey X, this is Matt Sencenbaugh and I'm with WrestlingIQ, did I catch you at a bad time?". This was a great interrupt, but also made me feel more human.
Last week my pitch was sales focused (this is my software, I'd like to schedule an appoint with you to demo it). This week I positioned myself as wanting to learn from the prospect (club wrestling coach) in question. I felt a lot more comfortable doing this.
Result was 2 voicemail, 2 dead phone numbers, and 2 pick ups. One pickup the person was no longer associated with the wrestling club, but the interaction went fine. No screaming or raging, just a simple one minute call to find out my info is out of whack.
The other pickup was helpful. The club coach explained to me how their team functions. How the website updating is handled, how the team messages their parents, etc. Critically we talked about how his team gets payment, practice space, and registrations through the city parks department. This fact means that my software is probably not a good fit for him, but it gave me more insider info into exactly what cut they are taking and what's good and bad about that. He also mentioned that he was considering moving away from the parks department, but had concerns about having to do all of that registration and payment stuff himself, which is exactly what my software is designed to handle. Case in point, he's not a good fit right now, but might be in the future.
I have a lot to learn, but this week was better than last week.